Ossining Vacations from ￥317,107
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The Latest Ossining Vacation Packages
Price found within the past 48 hours. Click for updated prices.
JW Marriott Essex House New York
Manhattan
￥347,068
per person
Jan 11 - Jan 16
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!
Reviewed on Oct 19, 2026
OYO Times Square
Manhattan
￥392,546
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
6.8/10 (2,123 reviews)
Great room friendly staff… only thing is house keeping came into our room 10:30 am when checkout was at 12 pm. They did it twice so be aware!
Reviewed on Oct 25, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
￥351,722
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The staff is incredible, and the hotel is very lovely and centrally located; everything was exactly as it appears in the photos.
Reviewed on Oct 25, 2026
Find the Best Ossining Vacation Packages
Ossining Hotel Deals
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
￥23,705
￥26,401 total
Nov 8 - Nov 9
includes taxes & fees
8.6/10 Excellent! (272 reviews)
"Beautiful grounds, not enough parking. Not enough towels, breakfast not available the day we came."
Reviewed on Oct 25, 2026
LIV Hotel Bronx - Newly Built
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
￥19,335
￥22,737 total
Nov 9 - Nov 10
includes taxes & fees
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
￥19,271
￥23,476 total
Nov 8 - Nov 9
includes taxes & fees
8.6/10 Excellent! (2,885 reviews)
"The dishes in the restaurant were dirty and the vending machine charges you $25 asa hold. And the bathroom smelled like mildew other than that stay was great"
Reviewed on Oct 25, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Ossining attractions
Travelers Rest
This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
Photo by louann ohora
Teatown Lake Reservation
This 1,000-acre nature preserve features diverse ecosystems along scenic trails. Explore the floating boardwalk across the lake for wildlife viewing and see the island's native wildflower collection.
Sing Sing Prison Museum
Step inside America's most infamous prison at the Sing Sing Prison Museum, opening in 2025 for its 200th anniversary. Explore artifacts and stories illuminating incarceration and rehabilitation in America.
Kitchawan Preserve
Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Louis Engel Waterfront Park
Louis Engel Waterfront Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Ossining Historical Society
This intimate museum preserves Ossining's heritage through artifacts connected to Sing Sing Prison and local history. Schedule a personalized appointment for the most enriching exploration of this community treasure.
Hudson Hills Golf Course
Nestled in Ossining's rolling terrain, this Mark Mungeam-designed course challenges players with strategic bunkers and undulating fairways. Enjoy Hudson River Valley views while navigating the thoughtful 18 holes.
Nelson Park
Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.
Frequently asked questions
How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination from ￥317,107 on Expedia. However, how much your vacation to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
The off-season is the best time to head to Ossining if you're hoping to keep costs down. Another tip for scoring cheap Ossining vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining vacation, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighborhoods like Town of Mount Pleasant and Pleasantville. If you've got some time to spare, add a tour or day trip to your Ossining vacation itinerary.
Is it worth booking a vacation package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining vacation off to a flying start by visiting top attractions like Louis Engel Waterfront Park.
How to find the best Ossining package deals?
Use Expedia's handy filters to find some tempting Ossining package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Ossining package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book an Ossining vacation as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Ossining?
If you have your Ossining travel dates locked in, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ossining?
- Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
- Budget wisely: Besides the price of your accommodations, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
- Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Ossining. Then, estimate how long you'll need at each, including any travel time.
- Bundle your accommodations and airfare: After you've settled on your dates and duration, lock in the ideal Ossining vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
